How to Get Your Ideal Holiday Schedule (or Close to It)

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November 25, 2015

There are few double-edged swords in American culture like the winter holiday season — which, it would seem, is on track to start in September within the next few years. It’s a great time to see family, and an even better time to refine your “avoid political conversation” skills. The holidays are a great distraction from the weather, and a reason to hate snowstorms that keep you from getting to dinner on time. It’s a great time to earn some extra cash, and the time of year that everyone wants off work. So how do you find the balance?

As a boss, there’s nothing worse than trying to schedule the holiday season. Everyone wants to be home with their families, and everyone is asking for the time off sooner and sooner. (Or, occasionally, at the very last minute.) Do you go solely on seniority? Do you let the early bird get the worms? Do you just close?

Do You Know What You're Worth?

You’re a Mean One, Mr(s). Boss

Maybe you’re OK with being the bad guy. If you’re not, here are a couple of creative ways for both you and your employees to figure out the right answer to make the holidays are truly wonderful time of the year:

1. Invest in Good Scheduling Software

If the current employee scheduling system at your workplace is something like the game Telephone, an elementary school art project, or that group chat you never check, you may consider investing in real scheduling software.

When I Work (full disclosure, I used to write for them), which is geared toward hourly employees, creates a space where employees can directly swap shifts with each other, put in requests, and get text alerts about upcoming hours.

2. Speak Up

You’ll never know who does or doesn’t want work during the holidays unless you ask.

On the employee side, If you want time off, don’t try to be secretive about it. Talk to your manager, and vocalize it to your fellow employees. Try to create a strategy to see if you can trade one holiday for another with someone who may have opposite plans from you.

3. Be Flexible

Ideally, you have a deadline by which your workers are supposed to submit their requests, but plans change. You don’t want to be a total Scrooge when one of your people asks you for an extra day closer to the holiday.

Remember that the most important thing is that you have coverage for the projects that matter, and that some dates (December 26, January 2) are generally a wash. If your report can get coverage, and you can keep things running without sacrificing your own holiday, consider granting the request. It’s the season of giving, after all.

For Workers: Make the Most of Your Time Off

No matter how flawless and compelling the advice in this article may be, you’re probably not going to get exactly what you wish for with your holiday schedule this year. But that’s OK, because there’s one last piece of wisdom that applies to everyone, manager and worker alike: learn how to maximize the time off that you do get.

Part of the problem with vacation in the U.S. is that we’re bad at taking it. We don’t unplug, get away from our inboxes, and actually enjoy the people we’re around. If you know you’re not going to get a lot of holiday time off, buy your gifts now so you’re not doing the shopping on that rare day off. Plan a “friends-giving” on some day that’s not the third Thursday of the month. Don’t let the man tell you when to celebrate. Take the season back: make your own damn holiday cheer.

Tell Us What You Think

Got some holiday gripes to get off your chest? What’s your trick for getting your desired days off? Let us know in the comments below or by joining the conversation on Twitter.